Kylie Jenner lent Timothée Chalamet a helping hand with his wardrobe just before they made their red carpet debut as a couple! French fashion maven and Tom Ford's creative director, Haider Ackermann, took to Instagram to share a mesmerizing array of photos and videos from their outing to the prestigious 70th David Di Donatello Awards in Rome on May 7th, Wednesday. Among these glimpses was a heartwarming behind-the-scenes moment where the two stars prepared together, painting a picture of camaraderie and mutual support.
Ackermann posted a screenshot from his FaceTime call with Jenner, 27, and Chalamet, 29, while they were in their hotel room, gearing up for the event. In the snap, Jenner, the founder of Kylie Cosmetics, could be seen meticulously rolling what seemed to be a lint roller over Chalamet's pristine white undershirt, as he beams with a charming smile.
Furthermore, Ackermann showcased a photo of Chalamet receiving the David for Cinematic Excellence honor, looking dashing in a Tom Ford ensemble – a sleek velvet suit paired over a black undershirt, adorned with a pristine white boutonniere. Accompanying this was a video capturing the couple's grand arrival on the red carpet.
Jenner complemented Chalamet's attire with a body-hugging, embossed dress featuring a dramatic plunging neckline from Schiaparelli's Fall/Winter 2025 collection. She accessorized her look with a velvet clutch adorned with gold embroidery and statement earrings from Schiaparelli, while her hair was sleekly styled in a chic bun, showcasing her dazzling jewelry.
"TEAMWORK - Miss K, you’re hired!!" Ackermann joked in the caption of his Instagram post. Turning his focus towards Chalamet, he penned, "BROTHER elegantly in TOM FORD receiving the 70th David Di Donatello Award. PROUD AS ALWAYS my Brother - H."
Jenner and Chalamet's grand night out followed shortly after the Kardashians star stole the spotlight at the 2025 Met Gala solo, while the actor stayed back to virtually cheer on a New York Knicks game in Boston. Jenner dominated the star-studded gala carpet in a custom Ferragamo gown, boasting a sheer corset bodice and a thigh-high slit. Conversely, Chalamet posted a cozy snapshot of himself watching the Knicks game in a gray hoodie.
The couple first sparked romance rumors in 2023, with a source telling PEOPLE that they were "spending time together and getting to know each other." They made their first public appearance at Beyoncé’s concert at the SoFi Stadium in Los Angeles in September of that year. Since then, they have been spotted on numerous dates, indulging in some PDA, including at a recent Lakers game in May.
Jenner accompanied Chalamet, who garnered multiple nominations for his role in A Complete Unknown, throughout the 2025 awards season, including the Golden Globes, BAFTAs, and Oscars.
